3-Nitrobenzaldehyde → [Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl ester

HRID 45810

Reaktionsgleichung

Reaktionsgleichung von HRID 45810
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:19][O:20][P:21]([O-:24])[O:22][CH3:23]>C(OCC)(=O)C>[CH3:19][O:20][P:21]([CH:7]([OH:8])[C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:24])[O:22][CH3:23]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 8471TriethylamineHCID 21884954Dimethylphosphite

Produkt 1

HCID 11299958[Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl esterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

3-Nitrobenzaldehyde (20 g, 0.132 mol) was dissolved in 100 mL of ethyl acetate. Triethylamine (22 mL, 0.158 mol, 1.2 eq) was added, followed by dimethylphosphite (15.7 mL, 0.171 mmol, 1.3 eq) and the mixture was stirred at room temperature. After 2 hours the mixture was diluted with 150 mL of ethyl acetate and washed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was treated with ethyl ether to obtain a beige solid, which was filtered and dried under vacuum at 40° C. for 1 h (26.7 g, 77% yield).

Aufarbeitung

  1. washwashed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was treated with ethyl ether
  5. customto obtain a beige solid, which
  6. filtrationwas filtered
  7. customdried under vacuum at 40° C. for 1 h (26.7 g, 77% yield)

Quellen und Nachweise

ORD-Eintrag
ord-6b6d0775abb64f6ba1883c5aa00c22cb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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